The winter packing series continues! So far, we’ve covered what to bring, how to fit it all in a carry on, and now it’s time to show you how I combine these pieces to make outfits for each day.
In case you need a quick refresher, we’re looking specifically at this packing list. My goal was to pack athletic clothes, weather clothes, fancy clothes, swimwear, and regular clothes (like PJs and travel clothes) all in one carry-on suitcase. The good news? It worked, and you can see the video proof right here.
So let’s jump into the daily looks I’ve created from the items in my suitcase:
DAY 1: TRAVEL + DINNER OUT
This travel outfit is easy and comfortable. I always feel put-together in a simple sweater, jeans, and big tote combo — and sunnies.
Once we land, I could throw on a long necklace, and this outfit will take me straight into dinner — no need to change.
To free up space in my carry on suitcase, I’m wearing my bulkiest items on the plane — including my black ankle booties and cognac cocoon coat.
Remember my friends Jess Lively of the Lively Show Podcast and Jessica Doll of Hej Doll from Wednesday’s post? If you haven’t bookmarked their blogs yet, you’ll want to right now. Both of them are travel pros, so I asked them for their sage advice on travel coats:
- Jessica Doll: I’ve had the Stadium-Cloth Cocoon Coat from J.Crew in black for years and it’s the perfect mix for warmth and style in a variety of scenarios. Though, if I’m going skiing or somewhere more adventurous I’d probably bring my Spiewak Aviation Eskimo Parka (it’s made with recycled down!).
- Jess Lively: Right now I only own one coat… so I’d have to go with that one! It is a mid-weight wool coat with a little leather detail on the sleeve. It’s similar to this one or this one.
DAY 2: HIKE + DINNER OUT
Woohoo! I’m most excited about this day because this girl loves day hikes. So I’ll be wearing yoga leggings, my base layer tee, Patagonia jacket, and running shoes. For a little color and interest, I’ll add my beanie on top.
I’m also bringing my swimsuit because we may stop at a hot springs on the way back. But even if not, hot tubbing is definitely on today’s agenda.
Later in the evening, we’re headed out to dinner — nice but not fancy, so I’ll dress up my jeans with my black ankle booties, crossbody bag, and long necklace. On top, I’ll add a little interest (and warmth) by layering my striped turtleneck underneath my black sweater. Finally, I’ll top it off with my cocoon coat.
DAY 3: SIGHTSEEING + NIGHT AT THE THEATRE
We’ll be walking around a ton today, plus it’s going to be cold and slushy, so I’m designing my outfit around comfortable, warm shoes — my weather boots.
(If you’re not into the duck boot look, here’s a sleeker waterproof bootie that can be dressed up, too.)
For the rest of the look, I’ll wear a base layer underneath my striped turtleneck. After yesterday’s hike, my base layer will definitely need a good steam with my sanitizing travel steamer or a quick wash in the sink. However, my turtleneck should still be nice and fresh since I only wore it to dinner last night.
Then, I’ll top it all off with my coat.
Later, we’ll be heading to the theatre for our fanciest night out, so I’m wearing my cashmere dress with coated leggings underneath, chic black ankle booties, and of course, my coat. I’ll also add a long necklace and my small black crossbody bag. This is my go-to look when I want to be dressed up but comfortable (leggings!) and warm (soft cashmere dress!). Win win.
DAY 4: MORE SIGHTSEEING + DOWNTOWN DINNER
Another day out and about in the cold and slush, so I’ll be back in my weather boots today. Even though these may not be the chicest of boots, they sure are comfortable, warm, and right for this particular trip.
I was curious about Jess + Jessica’s favorite travel shoes, so I asked them. Here’s what they had to say:
- Jessica: For city trips, my white Veja Esplar Sneakers are perfect. They’re flat, comfortable, and versatile. For more adventurous escapes, wool-lined duck boots like the UGG Cecile (I lived in these for my trip to Iceland).
- Jess: Brown leather booties! I can get a lot of wear out of a good pair of booties in cold city temps.
For dinner later, I’ll wear the same outfit but just swap the weather boots for my dressier black ankle booties, swap my day tote for my crossbody bag, and add a necklace.
However, if I did want to change and freshen up a bit for dinner, I could easily re-wear my theatre outfit from last night instead.
DAY 5: BRUNCH WITH FRIENDS + TRAVEL
Last day! In the morning, we’re grabbing brunch with some old friends at a cute little spot. Then it’s back to the airport for a day of travel.
I’m wearing the exact same outfit as Day 1 because (A) it’s a cozy, comfortable travel outfit and (B) I need to wear my bulkiest items on the plane to free up space in my carry-on suitcase.
KEEPING CLOTHES FRESH WHILE TRAVELING
Over the course of this trip, I’ll have worn my white sweater twice, my black sweater twice, and my striped turtleneck twice.
The key to making it work?
In my opinion, it’s all about three things: wearing base layers (it creates a barrier between your sweater and your skin, keeping sweaters cleaner, longer), using a steamer (steaming sanitizes clothes by actually killing any bacteria that might be lurking in the fibers — because of that, it can even remove faint odors), or giving your clothes a good ol’ hand washing in the sink.
But! How about another perspective? I asked Jess + Jessica how they keep their clothes clean when they travel. Here’s what they said:
- Jessica: As soon as I arrive at my destination and get settled, I unpack all of my clothing and hang it. I find that keeping it in my suitcase for the shortest amount of time possible helps with freshness, and wrinkles. If I have spare time or a special event, I take an iron to them on the first day as well.
- Jess: Staying in Airbnb’s with washers. : )
• • •
And there you have it!
Want to see the whole week’s worth of outfits in one simple graphic? Here you go! Feel free to save it or pin it for your future packing inspiration.
Tomorrow is the last post for the winter packing series, and it’s going to be a fun one! I’ll be sharing what I bring in my travel tote + how I keep it organized for the plane.
See you then!
Awesome post, Caroline! Definitely pinning for future reference… I always over pack!!
Laura @ http://www.thriveorsurvive.us
I love the coat. Do you have any tips about finding good, ethically made sweaters/coats that aren’t wool? I am sensitive to it and, it’s so hard to find beautiful outerwear that is not wool!
Hi Jamie! I really like the Jamie + the Jones line. Most of their sweaters are a heavy cotton, although really limited production, so they can be difficult to get your hands on. Hackwith Design House has some sweaters with lower wool content, so maybe that would be an option? Groceries Apparel, Patagonia, and Everlane would be worth looking at too. Good luck! :)
I’ve seen both you and Jess post about Veja sneakers, I love their sustainability and have been looking into getting a pair. How would you say are they comfort wise?
Hey Chelsea! They are great, no complaints here. My husbnad and I both have Vejas and they’ve held up pretty well too. :)
Carolyn Guy says
I am leaving in 11 days for a month long trip. When we arrive there it will be the end of their summer, and it is quite hot. How can I pack for a month?
If it were I, I would check first to see about the feasibility of washing clothes while on the trip. Then I’d look at which things in my closet could be easily washed, and how I often I want to do that. If you can do laundry once a week, then you only need to pack a week’s worth of clothing.
One thing I’ve noticed is that most fashion bloggers who give advice on packing usually (and wisely) recommend what Caroline does: plan out each day and each outfit. In reality, a lot of people don’t like to plan in that much detail. There’s no way I could get my husband to agree on a daily itinerary when we travel overseas–there are too many variables which will have to be evaluated after we arrive. For me, I have to take a simple variety & just be flexible while I’m there.
I think something similar is true for packing for a month. You can’t anticipate every single thing you’ll need. Best bet is to take a simple, flexible variety of clothing you know you are comfortable with–and then just do the best you can with what you’ve got.
Since you mention the weather, are wanting some ideas for warm-weather clothing? I think there are a lot of warm-weather packing lists on Pintrest. Caroline touches on an important point in this series when she mentions her wet-weather boots: If reasonable comfort conflicts with pure style, choose reasonable comfort. Just as important in hot weather as in cold!
Hey Carolyn! Sounds like fun. :) I agree with what MK said. How feasible is it that you’ll be able to do laundry? If it’s not a possibility, then you’ll have to be a bit more flexible with what you bring. Maybe not pack in a carry-on? I still think you can take a minimalist approach with it by mixing and matching items, and of course summer clothes don’t take up as much room as winter coats and boots — but it totally depends on other circumstances as well. Let us know how you do! Enjoy! :)
Kelly Boyce says
Great post and I loved the video. I’m keeping this in mind when we go away next.
Tanya E says
Wow, lots of good tips. It’s ages since I did much travelling (before kids) but still useful to see. Thank you for your video, yesterday, I used to roll stuff to pack, as less creases, but a good reminder, I have now kon-mari rolled 3 drawers: underwear, tops and my pyjama/loungewear/workout gear. I already had drawer dividers, but it all looks so organised now. I also put a whole lot of stuff away until spring…
Thanks too for the book recommendations ages ago, I am romping through the first Mistborn book (agenda have just ordered the next two). Great blog, just shows the best side of the internet when people share such good stuff.
Victoria B says
I really love seeing the outfits people put together for trips. It is my favorite part of packing series/posts. :) The only thing I would have done differently is to wear the duck weather boots on the plane as they seem like the bulkiest item, plus they will be dirty. I also might bring an extra pair of jeans since you have two days sightseeing with them and three dinners and it might be slushy and get them wet. But you could always wear the coated leggings for dinner instead one night and dry the jeans with a hair dryer, so it would be debatable. :) Have fun!
I’m usually just a lurker and never comment, but I’ve really enjoyed this series too much to stay silent! My husband and I are planning a trip to Iceland for our 10 year anniversary and this has been very refreshing on what I should pack to stay warm but not pay and arm and a leg in baggage fees. I loved the video yesterday and seeing all of the outfits laid out really puts it all together. Thank you and have a great trip!
I think your suggestions would really work! Thanks for sharing!
xx from Bavaria/Germany, Rena
I enjoyed this post, i like how you switched the outfits without to much trouble, the items are versatile and easy going, the footwear very comfy and the thing i liked the most was the fact that you used same items on first day as on the last because of the bulky items.
I am waiting for tomorrow as I think it may apply to the whole day by day usage if the tote, not only in the plane.
Thank you, Caroline!
Question: Did you carry a bag when your were hiking? I’m planning a similar trip and would be grateful to know…
Hey Shelly, no I didn’t carry one. Just my trusty water bottle :) I think a drawstring knapsack would be the easiest thing to squeeze into a carry-on though if you need one! :)
Thank you! I wouldn’t have thought of that…
Thanks for the post! I suggest taking along a scarf too, because if it’s cold enough to wear this coat, you’ll probably want some draft protection for walking around the city. Hope you have a great time! :)
That’s easy enough to squeeze in! Thanks for the suggestion, Christy! :)
Can you do a post on how you style and shoot photos to use in the Stylebook app? I love the app (and graphics like yours!) but I can never seem to get photos of my clothes that make me want to wear them …
Rylie, I have the exact same problem. Often when I take pictures of my clothes, I can hardly tell which pair of jeans or shirt this is when I use the app. I solved this problem by looking up images on the internet that are close enough to my actual clothes (for example look for grey T-Shirt). But it would be great to know how to take great pictures of my own clothes.
Melody smith says
I do the same thing as much as possible, find photos on the internet. If I wasn’t so lazy, I think my photos would turn out better taken in the daytime on a white background.
Melody smith says
I also try to find photos on the internet. And If I wasn’t so lazy, I think my photos would turn out better taken in the daytime on a white background. But I get in such a hurry, I take them in my closet & they’re not so great ?
Hey Rylie! Mimicking what they all said — Google Images for the win! :)
If I can’t find a picture on the web I never take pictures of my clothes directly in the app. Instead I import the picture from my iPhone album – which allows me to edit the photo first; make it brighter/darker etc.
Hope this can make it work a little better for you too.
Samantha Lee says
LOVE how you’ve put these outfit togethers and planned for the different events on your trip. Super helpful! I’ve started trying on entire outfits I plan to pack that way I know with 100% certainty that I will wear everything. :)
Just wondering, has anyone used any clothing sprays that help keep clothes smelling fresh? I don’t have a steamer but I’m trying to wear things a bit longer to save on laundry.
Hey Amy, I like this one for sweaters and freshening up: http://bit.ly/2jclCYF :)
This would be a great series to do in Spring and Summer!! Hope it continues :)
Alison langston says
Great post! I have these booties. I can’t seem to get the look right — wearing the booties with skinny/straight jeans. Any advice?
Hey Alison, here are a couple ways to style them!
Part 1: http://bit.ly/2k6i0tK
Part 2: http://bit.ly/2k1pRq0
I don’t know if the color of the jeans matters to you, but I tend to wear darker denim with them. And if you’re in a cold climate, you can also try tights for warmth — it also creates an easy transition on the eye from denim to boot! :)
Alison langston says
Thank you!! ?
Am I the only person wondering WHERE you are going?
Melody smith says
Thanks for this article! I’m spending 2 weeks in Europe in April (still cold there) & this gives me some great inspiration! And I ordered a steamer, so that will help ??
Two questions! What if you don’t know all the activities ahead of time and/or are unsure of weather in an unfamiliar place. I just got back from a trip to Peru and packing was a nightmare! I wish I’d had this guide at the time–it might’ve helped a little. We went for a wedding but there were a bunch of other potential activities, but I wasn’t really sure what was on the agenda…I ended up checking a medium suitcase and turns out I way overpacked, which was strestful in its own way.
Question two: where are you going?? You haven’t actually mentioned your wintery destination and i,m so curious!
Thanks for the great posts. I’m definitely pinning this for future packing dilemmas!
Hey Erika! When you don’t know the weather or activities, I think that would be the time to have grace with yourself and be a little more flexible with your packing. Of course you can still approach it from a minimalist aspect. Sometimes even just laying everything out in front of you will give you a better idea of what pieces can be mixed and matched and which ones you probably don’t need. Good luck! :)
love that you are making a whole series out of your travel style!
When reading this post, I just wondered why you would bring 2 sweaters and your cashmere dress – I was kind of thinking that you could make your cashmere dress work as a dark sweater as well (as you have shown on your 10×10 challenge)…
Also, wool and cashmere sweaters should be washed as little as possible (steaming, base layer or just hang it out in the fresh air works wonders as well) so I think it is totally OK to wear the same piece three times without washing it.
I hope this did not come across the wrong way – it was no criticism at all, more hoping to give something back to you with this idea. As a non-native speaker it is sometimes difficult to find the right words :) I really enjoy your blog and am thrilled about the video posts and more videos to come! Thank you for taking so much time, effort and dedication with your blog.
Caroline – I love the direction you’re taking with Un-Fancy and this post is really helpful!
Also, totally random side note but I wanted to tell you I finally bought the Halogen base layer long sleeve shirt you’ve been featuring, and this may be terrible to admit but I don’t think I’ve taken it off except to shower since it came in the mail a few days ago. That’s not really true, thankfully, but I’ve been wearing it a lot! It is so comfy and soft! And it doesn’t lose its shape! Thanks so much for the recommendation. I used to buy a bunch of long sleeve layer shirts but now I feel like I only need this one. :-)
Caroline, you have changed my entire perspective on packing for travel – I can’t believe that I am actually excited to pack and plan outfits with minimalist style. These travel posts with packing lists and day-by-day outfit ideas are pure gold, and always my favorite to bookmark and go back to when I have an upcoming trip. Your selections are versatile and essential; they help me to think of similar options from my own closet without needing to shop for new vacation outfits, which is always a temptation. It’s amazing how much time and energy I save when planning a trip these days, but the greatest gift of this process is that I am able to be much more present and enjoy my time away like I’ve always wanted to, rather than fuss over what to wear. Just amazed, and so thankful for your perspective!
I am currently packing for 19 days in a Osprey Porter 46L backpack (it is a pretty good size because it is all one compartment but still a small carry on size). We will be in Chile with varying weather and activities so I have had to think hard on this one. It is certainly challenging but it can be done! I had been a notorious over packer up until recently. I have also been a flight attendant for 9 years and travel all the time for fun too. Just goes to show anyone can be bad at packing and use the help. What has really helped are blogs like this which made me realize I had such a hard time packing because my wardrobe was all over the place. I would want to bring something on a trip that I don’t even wear in real life. This is just never a good idea for me. Now that I have stream lined my entire wardrobe it makes packing so much easier. Everything is easier now that I have reduced the closet clutter.
Love your blog and these packing posts. Thank you Caroline!
Hi Caroline! Love the post. I do have a random question though…what size do you wear in your Wilfred coat? I waited far too long to order one, and now they only have XXS and XS available, and I’m not sure I can swing an XS. Would you mind sharing what size yours is and any details about the fit? Thanks a bunch!
Hi Whitney! In my experience, they run a bit large. I ordered an XXS so it would be more fitted. If you wanted to wear bulkier clothes underneath, I would go with your regular size. Hope that helps! :)
Late to the party as I am just discovering your blog! I was wondering if you have any advice on steamers for while traveling?
Hey Christine! I sure do! This is my go-to: http://bit.ly/2fi7v4x :)